DE2447735A1 - Spiro-cyclopropane, verfahren zu ihrer herstellung und ihre verwendung zur schaedlingsbekaempfung - Google Patents
Spiro-cyclopropane, verfahren zu ihrer herstellung und ihre verwendung zur schaedlingsbekaempfungInfo
- Publication number
- DE2447735A1 DE2447735A1 DE19742447735 DE2447735A DE2447735A1 DE 2447735 A1 DE2447735 A1 DE 2447735A1 DE 19742447735 DE19742447735 DE 19742447735 DE 2447735 A DE2447735 A DE 2447735A DE 2447735 A1 DE2447735 A1 DE 2447735A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- phenoxy
- spiro
- dimethyl
- represent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000004480 active ingredient Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- -1 phenoxy-substituted phenyl group Chemical group 0.000 claims description 10
- 239000000575 pesticide Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 4
- 239000008187 granular material Substances 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000004546 suspension concentrate Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000443 aerosol Substances 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- 150000001942 cyclopropanes Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000255969 Pieris brassicae Species 0.000 description 4
- 230000000895 acaricidal effect Effects 0.000 description 4
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 241000171293 Megoura viciae Species 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 241001454293 Tetranychus urticae Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 235000016068 Berberis vulgaris Nutrition 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 241001608567 Phaedon cochleariae Species 0.000 description 2
- 241000256248 Spodoptera Species 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- AFEOKIGLYCQHAZ-UHFFFAOYSA-N (5-benzylfuran-3-yl)methanol Chemical compound OCC1=COC(CC=2C=CC=CC=2)=C1 AFEOKIGLYCQHAZ-UHFFFAOYSA-N 0.000 description 1
- UJUNUASMYSTBSK-UHFFFAOYSA-N 1-(bromomethyl)-3-phenoxybenzene Chemical compound BrCC1=CC=CC(OC=2C=CC=CC=2)=C1 UJUNUASMYSTBSK-UHFFFAOYSA-N 0.000 description 1
- IYVKHCOVGKGJDP-UHFFFAOYSA-N 1-benzyl-3-(chloromethyl)benzene Chemical compound ClCC1=CC=CC(CC=2C=CC=CC=2)=C1 IYVKHCOVGKGJDP-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- NSAYSEQSQBVPPF-UHFFFAOYSA-N C1CC1.C1(CC1)C(=O)O Chemical compound C1CC1.C1(CC1)C(=O)O NSAYSEQSQBVPPF-UHFFFAOYSA-N 0.000 description 1
- 102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4692673A GB1437987A (ja) | 1973-10-08 | 1973-10-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2447735A1 true DE2447735A1 (de) | 1975-08-21 |
Family
ID=10443099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742447735 Withdrawn DE2447735A1 (de) | 1973-10-08 | 1974-10-07 | Spiro-cyclopropane, verfahren zu ihrer herstellung und ihre verwendung zur schaedlingsbekaempfung |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3950535A (ja) |
| JP (1) | JPS5821885B2 (ja) |
| AR (1) | AR215115A1 (ja) |
| BE (1) | BE820418A (ja) |
| BR (1) | BR7408318A (ja) |
| CA (1) | CA1052797A (ja) |
| CH (1) | CH608170A5 (ja) |
| DD (1) | DD115841A5 (ja) |
| DE (1) | DE2447735A1 (ja) |
| EG (1) | EG11527A (ja) |
| ES (1) | ES430753A1 (ja) |
| FR (1) | FR2246533B1 (ja) |
| GB (1) | GB1437987A (ja) |
| HU (1) | HU172534B (ja) |
| IL (1) | IL45795A (ja) |
| IT (1) | IT1046668B (ja) |
| NL (1) | NL7413166A (ja) |
| OA (1) | OA04790A (ja) |
| TR (1) | TR18223A (ja) |
| ZA (1) | ZA746362B (ja) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2605828A1 (de) * | 1975-02-13 | 1976-08-26 | American Cyanamid Co | Phenoxybenzylester von spirocarbonsaeuren |
| EP0006456A1 (de) * | 1978-06-09 | 1980-01-09 | Bayer Ag | Spiropentancarbonsäureester, Verfahren zu deren Herstellung, insektizide und akarizide Mittel, Verwendung der Spiropentancarbonsäureester zur Bekämpfung von Insekten oder Spinnentieren und Verfahren zur Herstellung insektizider oder akarizider Mittel |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4060632A (en) | 1975-02-13 | 1977-11-29 | American Cyanamid Company | Method for controlling acarina |
| US3966959A (en) | 1975-02-13 | 1976-06-29 | American Cyanamid Company | Insecticidal and acaricidal, pyrethroid compounds |
| GB1577136A (en) * | 1976-03-22 | 1980-10-22 | Shell Int Research | Cyclopropane carboxylate ester derivatives and their use as pesticides |
| US4118510A (en) * | 1976-03-22 | 1978-10-03 | Shell Oil Company | Dispirocyclopropane carboxylate pesticides |
| GB1580193A (en) * | 1976-04-22 | 1980-11-26 | Nat Res Dev | Phenyl acetic acid derivatives |
| US4221812A (en) * | 1978-02-09 | 1980-09-09 | Ciba-Geigy Corporation | Pesticidal spiropentanecarboxylates |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS515450B1 (ja) * | 1971-06-29 | 1976-02-20 |
-
1973
- 1973-10-08 GB GB4692673A patent/GB1437987A/en not_active Expired
-
1974
- 1974-08-30 CA CA208,231A patent/CA1052797A/en not_active Expired
- 1974-09-27 BE BE1006199A patent/BE820418A/xx not_active IP Right Cessation
- 1974-09-30 US US05/510,197 patent/US3950535A/en not_active Expired - Lifetime
- 1974-10-04 DD DD181521A patent/DD115841A5/xx unknown
- 1974-10-04 IT IT28088/74A patent/IT1046668B/it active
- 1974-10-07 TR TR18223A patent/TR18223A/xx unknown
- 1974-10-07 OA OA55316A patent/OA04790A/xx unknown
- 1974-10-07 JP JP49114789A patent/JPS5821885B2/ja not_active Expired
- 1974-10-07 FR FR7433630A patent/FR2246533B1/fr not_active Expired
- 1974-10-07 NL NL7413166A patent/NL7413166A/xx not_active Application Discontinuation
- 1974-10-07 HU HU74SE00001747A patent/HU172534B/hu unknown
- 1974-10-07 CH CH1344174A patent/CH608170A5/xx not_active IP Right Cessation
- 1974-10-07 AR AR155954A patent/AR215115A1/es active
- 1974-10-07 ZA ZA00746362A patent/ZA746362B/xx unknown
- 1974-10-07 DE DE19742447735 patent/DE2447735A1/de not_active Withdrawn
- 1974-10-07 BR BR8318/74A patent/BR7408318A/pt unknown
- 1974-10-07 ES ES430753A patent/ES430753A1/es not_active Expired
- 1974-10-07 IL IL45795A patent/IL45795A/xx unknown
- 1974-10-08 EG EG456/74A patent/EG11527A/xx active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2605828A1 (de) * | 1975-02-13 | 1976-08-26 | American Cyanamid Co | Phenoxybenzylester von spirocarbonsaeuren |
| EP0006456A1 (de) * | 1978-06-09 | 1980-01-09 | Bayer Ag | Spiropentancarbonsäureester, Verfahren zu deren Herstellung, insektizide und akarizide Mittel, Verwendung der Spiropentancarbonsäureester zur Bekämpfung von Insekten oder Spinnentieren und Verfahren zur Herstellung insektizider oder akarizider Mittel |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1052797A (en) | 1979-04-17 |
| EG11527A (en) | 1977-08-15 |
| AU7400474A (en) | 1976-04-08 |
| JPS5821885B2 (ja) | 1983-05-04 |
| IT1046668B (it) | 1980-07-31 |
| GB1437987A (ja) | 1976-06-03 |
| BE820418A (nl) | 1975-03-27 |
| US3950535A (en) | 1976-04-13 |
| HU172534B (hu) | 1978-09-28 |
| CH608170A5 (ja) | 1978-12-29 |
| OA04790A (fr) | 1980-08-31 |
| FR2246533B1 (ja) | 1978-03-24 |
| NL7413166A (nl) | 1975-04-10 |
| IL45795A (en) | 1978-01-31 |
| ES430753A1 (es) | 1977-05-16 |
| JPS5062957A (ja) | 1975-05-29 |
| BR7408318A (pt) | 1976-04-27 |
| DD115841A5 (ja) | 1975-10-20 |
| TR18223A (tr) | 1976-11-25 |
| ZA746362B (en) | 1975-11-26 |
| AR215115A1 (es) | 1979-09-14 |
| IL45795A0 (en) | 1974-12-31 |
| FR2246533A1 (ja) | 1975-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal |